Water → 2-benzyl-6-bromo-3-(1-hydroxyethyl)-4-phenyl-2H-isoquinolin-1-one

HRID 750264Notes

Reaction equation

HRID 750264 reaction equation
[CH2:1]([N:8]1[C:17]([CH:18]=[O:19])=[C:16]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([Br:26])[CH:14]=2)[C:9]1=[O:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:28][Mg]Br.O>C1COCC1>[CH2:1]([N:8]1[C:17]([CH:18]([OH:19])[CH3:28])=[C:16]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([Br:26])[CH:14]=2)[C:9]1=[O:27])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 230605422-Benzyl-6-bromo-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carbaldehydeHCID 178418573HCID 178418573, compound

Product 1

HCID 230610042-benzyl-6-bromo-3-(1-hydroxyethyl)-4-phenyl-2H-isoquinolin-1-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-benzyl-6-bromo-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carbaldehyde (500 mg) in THF (5 ml) was added dropwise a solution of methyl magnesium bromide in THF (3M, 0.5 ml) at room temperature, and the mixture was stirred for 10 min. To the reaction mixture was added water and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was crystallized from ethyl acetate-hexane to give the title compound (470 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe obtained residue was crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-8d0ccb074a4446f2b43f206f6a5eaff8
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

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